Paul Klee's art found broad impact upon philosophers of varying commitments, including Hans-Georg Gadamer. Moreover, Klee himself was not only one of the most important artists of aesthetic modernism but one of its leading theoreticians, and much in his work, as in Gadamer's, originated in post-Kantian literary theory's explications of symbol and allegory. Indeed at one point in
Truth and Method
, Gadamer associates his project for a general "theory of hermeneutic experience" not only with Goethe's metaphysical account of the symbolic but equally with a "rehabilitation" of allegory. In this paper, I examine this position and Gadamer's own use of it in his analysis of Klee's work, contrasting it with that of Walter Benjamin's account of allegory, equally indebted to Goethe and this archive. Finally, I contrast the resulting interpretations of Klee, discussing the implications that evolve for understanding both Gadamer and Benjamin— but equally for understanding Klee's work and, provisionally, the work of art, thus construed, for philosophy.